What Do People Regret Most Before They Die? What I Learned When Death Stopped Being Theoretical

The Question You Don't Let Yourself Ask Until You Have To

There is a question most people defer for decades. They know it's waiting for them somewhere down the road — in a hospital room, maybe, or in the quiet of a sleepless night after a diagnosis arrives that rearranges everything. The question is this: if I knew I was running out of time, what would I regret most? Most of us don't ask it. We keep our heads down, stay busy, and tell ourselves there's plenty of time to sort out what actually matters. Then something happens that strips that illusion away, and suddenly the question isn't abstract anymore. It's the only thing in the room.

I am not writing this as someone who read about mortality in a philosophy book. I am writing this as someone who has sat with that question in ways I didn't choose and couldn't ignore. I worked on Wall Street for years inside a culture that treated time as a currency to be spent on production — not on living, not on relationships, not on any of the things people list when they're finally honest about what they wished they'd done more of. And I survived September 11th, 2001, by a margin that still stops me cold when I think about it. My colleagues at Cantor Fitzgerald didn't make it out of One World Trade Center. They were at their trading desks on the 104th floor when the world changed. I wasn't there that day only because of a chance decision — the randomness of a single turn that sent my life in a different direction. That kind of near-miss doesn't leave you. It lives in you. It asks you, over and over, what you're doing with the time you were given when they were not.

What I've come to understand — slowly, imperfectly, and only after enough setbacks that I couldn't rationalize my way around them — is that the regrets people carry at the end of life are not the ones we spend our working years trying to avoid. We spend our careers trying not to fail. We optimize against financial regret, professional regret, the regret of not achieving enough. But the research, and the lived experience of anyone who has stared down mortality, tells a very different story. The things people regret most have almost nothing to do with what they accomplished. They have everything to do with how they lived, who they showed up for, and how fully they inhabited their own existence.

What the Research Says — and Why Most People Dismiss It

The body of research on end-of-life regret is both consistent and quietly devastating. Palliative care workers, hospice nurses, and researchers who spend time with people in the final chapters of life report the same themes emerging again and again. The most famous account comes from Bronnie Ware, a palliative care nurse whose documentation of the most common regrets of the dying has reached millions of people around the world. Her findings are not complicated. They're almost unbearably simple. The most common regret is this: I wish I'd had the courage to live a life true to myself, not the life others expected of me. The second is one men in particular report with striking frequency: I wish I hadn't worked so hard. The third is about authenticity in relationships — wishing for the courage to have expressed true feelings rather than suppressing them to keep the peace. The fourth is about friendships that faded because they were never nurtured. And the fifth is about happiness — the recognition, arriving too late, that happiness is a choice, and that far too much of life was spent waiting for the conditions to be right before allowing it.

What strikes me about this list is not its content — it's how predictable it is, and how thoroughly we ignore it. Every person reading this already knows, on some level, that working less and connecting more is probably the right answer. They know that living for external approval is a slow erosion of the self. They know that friendships require effort and presence. None of this is new information. And yet the research keeps confirming the same regrets, decade after decade, because knowing the right thing and actually reorganizing your life around it are two profoundly different acts. The gap between understanding and living is where most of a human life gets spent.

What makes this worse is the specific culture many high achievers inhabit. Wall Street — and by extension the broader world of high-performance careers in finance, law, medicine, and tech — runs on a mythology that treats every hour not spent producing as a moral failing. I lived inside that mythology long enough to have internalized it completely. The culture around me wasn't just tolerant of overwork; it was reverent toward it. The person who left at 6 p.m. was suspect. The person who answered emails at midnight was a warrior. The totality of your worth as an individual was, in a very real way, your net worth. I've written about this in Terminal Success by Jason Mandel because it took me years to understand how thoroughly that framework had colonized the way I thought about my own life — and how much it was costing me in the currency that actually matters.

The Morning That Changed Everything I Thought I Knew About Time

On September 11th, 2001, I was not at my desk at One World Trade Center. I had left Cantor Fitzgerald by that point — an ordinary sequence of decisions that I couldn't have known, at the time, amounted to a reprieve. The friends and colleagues I'd worked alongside on the 104th floor didn't walk out of that building. They were there at their desks, doing what we all did — working hard, building something, moving toward whatever came next. And then there was no next. They died eighty-seven days before the sixtieth anniversary of another sudden and deliberate attack against America, and I have thought about them — about the arithmetic of survival and loss — more times than I could count.

What September 11th gave me — and I say gave deliberately, even though that word feels wrong against something so enormous — was the permanent removal of the idea that time is abundant. Before that day, I treated time the way most high achievers do: as a resource to be maximized, scheduled, and squeezed. After it, I couldn't maintain that fiction. The people I'd worked with hadn't run out of ambition or talent or plans. They'd run out of time in a way that had nothing to do with how hard they worked or how much they'd built. And whatever version of themselves they'd been deferring — the version that would slow down, the version that would be present, the version that would finally do the things that mattered beyond the office — that version never got its chance.

I didn't transform overnight. That would be a cleaner story, but it wouldn't be true. The truth is that the understanding arrived slowly, and kept arriving, in waves — each one pushing me a little further from the operating assumption that achievement was the same thing as a life well-lived. The near-miss planted a seed. The years that followed, with their own pressures and diagnoses and confrontations with the limits of a driven life, watered it. What grew was a different relationship with time — not relaxed, not passive, but deeply intentional. A recognition that every day that proceeds without asking what it's actually for is a day that moves in a direction you may not have consciously chosen.

Why High Achievers Are Particularly Vulnerable to the Wrong Regrets

Here is something that rarely gets said plainly: high achievers are not more likely to live well. They are often less likely to, because the same traits that drive achievement — persistence, discipline, the capacity to delay gratification, the tolerance for sustained discomfort — also make it extraordinarily easy to defer the things that matter most indefinitely. The high achiever always has a reason to push through. There's another quarter, another milestone, another target just ahead that will justify the sacrifice. The sacrifice gets normalized, and then extended, and then calcified into a way of life that the person inside it can no longer see clearly because it's simply become the air they breathe.

The specific shape of the high achiever's regret is usually not about wishing they'd worked harder. It's about wishing they'd been present. Wishing they'd been there — actually there, not physically present but mentally somewhere else — for the moments they can't recover. The child's performance they attended while composing a mental memo. The dinner where their body was at the table but their attention was on the deal. The vacation that was really just a remote office with better scenery. These aren't dramatic failures. They're quiet ones, accumulated invisibly, until one day there's enough distance to see the pattern and understand what it cost.

Wall Street sharpens this particular vulnerability to a fine edge. The culture I was part of didn't just tolerate this kind of absence — it rewarded it. The person who was fully present in their family's life at the expense of the firm's needs was not celebrated. The person who sacrificed that presence for the firm was. Over time, you stop noticing the sacrifice because it's so thoroughly normalized. You stop asking whether the trade-off is worth it because the culture has already answered that question for you, and the answer is always the same: yes, of course it is. You're building something. You're winning. This is what winning requires. And maybe it does — maybe the version of winning that culture was offering did require it. What it didn't offer was a clear accounting of what that version of winning would eventually cost.

The Deathbed Test Nobody Wants to Take Early

There is a thought exercise that has appeared in various forms in business literature, in psychology, in philosophy, and in spiritual traditions across cultures: imagine yourself at the end of your life, looking back. What do you want to have been true? What do you want to have done, experienced, built, given? Who do you want to have been to the people who mattered most? Now work backward from that vision to the choices you're making today. Are they pointing in that direction — or in a different one?

Most people find this exercise uncomfortable. Not because it's difficult, but because it's clarifying. It cuts through the day-to-day rationalizations and the quarterly pressures and the ambient noise of ambition, and it presents a much simpler question: is the life you're living the one you'll be glad you lived? For a lot of high achievers, when they sit with that question honestly, the answer is complicated in ways they'd rather not examine. Because the life they're building on paper — the career trajectory, the financial accumulation, the professional status — and the life they'd endorse from a deathbed vantage point are often significantly different things. One is optimized for what the culture around them values. The other is optimized for something quieter and more personal and harder to explain to anyone who hasn't already asked the question.

I have taken that test in circumstances I did not choose — in the aftermath of 9/11, in the middle of health scares, in the kind of sleepless early morning hours that strip away the performance and leave you with just the raw accounting of what you've done with your days. What I found, each time, was a version of myself that knew the answer clearly and a version of myself that was very skilled at avoiding it. The distance between those two versions is something I write about, explore, and return to — because I think that distance is where most of the important work of a meaningful life happens. Not in the achievements, but in the narrowing of that gap.

What People Actually Regret — And What They Almost Never Regret

It is worth spending time on something the regret research almost universally confirms, because it runs so directly counter to the anxieties that govern most high-achieving lives: almost nobody, at the end of their life, regrets not having worked more. The person lying in a hospital bed with a clear view of the finish line does not typically wish they'd spent more hours at the office, taken more conference calls, or pushed harder for the next promotion. What they regret is the opposite — the presence they traded away in service of that work, the relationships they let thin out, the moments they were too distracted or too exhausted to inhabit.

Similarly, almost nobody reports regretting having been too generous with their time. Too available to the people they loved. Too willing to step away from the desk and be present in their actual life. The regrets run heavily in the other direction. They are regrets of omission — of things not said, relationships not maintained, experiences not had, selves not fully expressed. They are regrets about having worn a mask so long that they lost track of the face underneath it. They are regrets about having let the culture of achievement define their worth so completely that they never paused long enough to develop an independent answer to the question of what made their life meaningful.

What almost nobody regrets is the money they didn't make. The deal that didn't close. The position they didn't take. The bonus that came in lighter than expected. These are the things that generate enormous anxiety during the working years — the things that keep people at their desks past midnight, that drive the competitiveness and the sacrifice and the erosion of everything outside the work. But at the end of the line, they almost never appear on the list of what mattered. The financial accumulation that felt so urgent and so definitional during the years of building it tends to look very different from the vantage point of a life nearly fully lived. Not worthless, exactly. But not what mattered most, either. And the price paid to accumulate it — in time, in presence, in relationships, in health — that price is often the source of the deepest grief.

Living Forward From This Understanding

The honest version of what I've learned is that you cannot fully absorb this understanding from the outside. You can read the research. You can hear the stories. You can nod along to every word of this article. And then you can close the browser and go straight back to the habits and the pressures that pull in the opposite direction, because the culture you're embedded in is powerful and continuous and it doesn't stop pulling just because you had a quiet insight on a Sunday afternoon. The insight fades. The inbox doesn't.

What actually moves people — what I have seen shift something real in myself and in the people I've spoken with who have done this work — is not information. It's experience. Specifically, it's the experience of being close enough to the end of something to feel the weight of what was spent getting there. The near-miss. The diagnosis. The loss. The moment when the theoretical becomes actual and you understand, in your body rather than your mind, that time is finite and the choices you make about it are the most consequential choices of your life. I wish I could hand that understanding to someone without the accompanying cost. I haven't found a way to do that. What I can do is try to describe it clearly enough that some small portion of the work gets done before the crisis rather than after it.

The practical question — which deserves a real answer rather than a motivational platitude — is what to actually do with this understanding. Not as a grand reinvention, but as a daily practice. The answer I've arrived at is not about radical life changes, though sometimes those are warranted. It is about developing an honest, ongoing conversation with yourself about the gap between the life you're living and the life you'd endorse from that deathbed vantage point. Not to generate guilt, which is useless, but to generate course corrections — small and consistent — in the direction of what actually matters to you when you strip away the performance and the external expectations and the noise of the culture telling you what success looks like.

The Question That Stays With You

My colleagues at Cantor Fitzgerald did not get to ask the end-of-life questions from a bed with time to reflect. They got no warning, no transition, no opportunity to reorganize their lives around what mattered most. That reality — that most of us assume we'll have time to get it right eventually, and that assumption can be wrong in an instant — is something I have not been able to set down. It sits with me in a way that has changed how I move through days, how I think about work and presence and the things I choose to show up for. Not perfectly. Not always. But with a level of intentionality that didn't exist before I had to sit with what their absence meant.

In Terminal Success by Jason Mandel, I write about the accumulation of these confrontations with time and mortality — 9/11, health, the particular disorientation of achieving what you set out to achieve and finding it less sustaining than you expected. The through line in all of it is the same question: what is all of this for? Not as a nihilistic question, but as an honest and urgent one. Because the answer you give to that question — the real answer, not the one you perform for your industry — determines what your life actually looks like when you add it all up. It determines what you'll carry with you into whatever quieter chapter eventually arrives. And it determines whether the story you tell yourself about why you worked so hard, sacrificed so much, and deferred so many things will hold up when the performance is over and there's nothing left to defend it but the truth.

Nobody asks these questions too early. That's the only thing I know for certain about them. Every person I've spoken to who has been through a genuine confrontation with mortality — who has sat in that silence where the usual noise falls away — says the same thing: they wish they had asked sooner. They wish they hadn't needed the crisis to see clearly. They wish the understanding had arrived before the urgency did. That's the only gift in writing something like this. Not an answer — I don't have a clean one to offer. Just the invitation to ask the question before you have to.

Frequently Asked Questions

What do people regret most before they die?

The most consistently reported regrets at the end of life involve not how much someone achieved, but how they chose to live. Research and accounts from palliative care workers point to the same themes: wishing they'd lived more authentically rather than according to others' expectations, wishing they hadn't spent so much of their life working at the expense of presence and relationships, wishing they'd expressed their feelings more freely, and wishing they'd maintained the friendships and connections that gradually faded under the pressure of a driven life. Almost nobody reports wishing they had worked more or earned more. The regrets are almost entirely about presence, authenticity, and connection — the things that are hardest to prioritize inside a culture that rewards production above all else.

How does surviving a near-death experience change your priorities?

In my own experience — and in what research on post-traumatic growth consistently finds — surviving a near-death experience doesn't automatically reorganize your priorities. The change is more gradual and more complicated than that. What it does do, almost universally, is remove the comfortable assumption that there is infinite time to sort out what matters. That assumption is the foundation of most deferral — the idea that you'll have space, eventually, to slow down, to be more present, to build the relationships and the life that keeps getting postponed. A near-miss with death pulls that foundation out, and what you're left with is the urgent, undeniable reality that right now is all that's guaranteed. For some people that leads to immediate and dramatic change. For most of us, it leads to a long, ongoing renegotiation with the habits and the culture that have been pulling us in the wrong direction.

Why do high achievers tend to regret overworking?

Because the skills that make high achievers successful — the ability to delay gratification, to sustain effort over long periods, to keep pushing through discomfort — are also the skills that make it very easy to defer everything outside the work indefinitely. High achievers are exceptionally good at rationalizing sacrifice. There is always another goal, another milestone, another justification for why right now is not the time to slow down or be present or invest in the relationships and experiences that don't show up on a performance review. The tragedy is that those justifications are almost always available. There is never a shortage of reasons to keep going. And by the time the achievement arrives that was supposed to make the sacrifice worthwhile, the things that were sacrificed to get there are often no longer available in the same form — the children are older, the relationships have cooled, the health has changed, the years are simply gone.

Does success make end-of-life regret worse?

In some ways, yes. People who have sacrificed the most in pursuit of achievement sometimes arrive at the end of their lives with the clearest view of what the trade-off actually cost, because the contrast between what they built and what they gave up is so stark. Financial success, professional accomplishment, and status do not insulate against regret — and there is research suggesting that people who achieved high levels of external success by conventional measures sometimes carry heavier regret about the personal costs than people who achieved less but lived with more balance and presence. The success doesn't cancel the cost. It sometimes makes the cost more visible.

How do I stop deferring the things that matter most?

The honest answer is that stopping is less about willpower or decision-making than it is about developing a practice of honest self-examination. The most useful thing I've found is returning regularly to what I think of as the deathbed test — imagining yourself at the end of your life, looking back, and asking whether the choices you're making now are pointing toward the life you'd endorse from that vantage point. Not as a guilt exercise, but as a navigation tool. Small, consistent course corrections over time are more durable than dramatic reinventions. You don't have to blow up your career or abandon your ambitions. You do have to stop pretending that the things you keep deferring will still be available when you finally get around to them. Some of them will be. Some of them won't. The skill is learning to tell the difference — and choosing, again and again, to show up for the ones that can't wait.